Supplementary Material for Chemical Communications
This journal is © The Royal Society of Chemistry 2003
Supplementary Information
(ButO)3SiOSi(CH3)2Cl II. A tetrahydrofuran solution (20 ml) of tris(tertiarybutoxy)silanol (8.0 g, 30 mmol) and pyridine (2.4 g, 30 mmol) was slowly added to a
stirring ice cooled solution (25 ml) of dichlorodimethylsilane (7.5 g, 58 mmol). The
reaction mixture was slowly warmed to room temperature after addition and was
stirred for 8 h. The pyridine hydrochloride white solid was filtrated and washed with
150 ml of tetrahydrofuran. The solvent was then removed from the filtrate in vacuo.
Pentane was then added to the remaining liquid and the mixture was then filtered.
Removal of pentane from the solution afforded 10.2 g of II in 94 wt.% yield.
Elemental analysis found 46.68% C, 9.62% Cl, and 9.22% H (compared with
theoretical 47.1% C, 10% Cl, and 9.3% H).
(ButO)3SiOSi(CH3)2OSiPh2OH III. To a stirred solution of
diphenylsilanediol (12.5 g, 57 mmol) and pyridine (2.23 g, 29 mmol) in
tetrahydrofuran (75 ml) was added a solution of II (10.0 g, 28 mmol) in
tetrahydrofuran (30 ml) in an ice bath. The resulting reaction mixture was slowly
warmed up to room temperature and further stirred overnight. The white pyridine
hydrochloride solid was removed by filtration and washed, and the washed liquid was
added to the filtrate. The combined filtrate was dried by evacuation. The solid
product was extracted with pentane (50 ml) three times and the unreacted
diphenylsilanediol solid was filtered out. 13.2 g of the product was obtained in 80
wt.% yield after removal of pentane in vacuo. Elemental analysis found 58.49% C
and 8.07% H (compared with theoretical 58.3% C, and 8.2% H).
(OtBu)3SiOSi(CH3)2OSiPh2OSi(CH3)2Cl IV. At 0°C, 2.1 g (4 mmol) of III
and 0.3 g (4 mmol) of pyridine in tetrahydrofuran (10ml) was added slowly to a
vigorously stirred solution of dichlorodimethylsilane (0.95 g, 8 mmol) in 10 ml of
tetrahydrofuran. The reaction mixture was warmed to room temperature and stirring
was continued for 8 h. The pyridine hydrochloride was then separated by filtration
and washed with 50 ml of tetrahydrofuran. After removal of the volatile material from
the combined filtrate and extracts, pentane was then added to the remaining liquid and
the mixture was then filtrated. 2.14 g of IV (95.5 wt.% yield) was obtained after
removal of pentane from the solution. Elemental analysis found 54.65% C, 3.98% Cl,
and 7.87% H (compared with theoretical 53.4% C, 5.7% Cl, and 7.8% H).
(OtBu)3SiOSi(CH3)2OSiPh2OSi(CH3)2OSiPh2OH V. Compound V was
prepared by slowly adding a tetrahydrofuran (10 ml) solution of IV (2.14 g, 3.5
mmol) to the ice cooled stirring solution of diphenylsilanediol (1.5 g, 6.9 mmol) and
pyridine (0.28 g, 3.5 mmol) in tetrahydrofuran (10 ml). After separation of pyridine
hydrochloride from the solution, the solvent was removed in vacuo, leaving a wetlooking white solid. Extraction of V with pentane and separation of unreacted
diphenylsilanediol from the solution gave a clear solution. Removal of pentane in
vacuo produced 2.47 g of V (89.8 wt.% yield). Elemental analysis found 58.07% C
and 7.23% H (compared with theoretical 59.4% C, and 7.4% H).